triphenylphosphine in tetrahydrofuran; water T=20°C; Reduction; Staudinger reaction; 12 h;

1: (1S,2S)-trans-2-azidocyclopentanol With triphenylphosphine in tetrahydrofuran; water T=20 - 65°C; 6 h; 2: di-tert-butyl dicarbonate With triethylamine in tetrahydrofuran; water T=20°C; 3 h;

1: H2 / PtO2 View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209320', constants.ctx, '0')">sodium azide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4371014', constants.ctx, '0')">ammonium chloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=60&deg;C;&nbsp;13&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '10775048', constants.ctx, '0')">titanium(IV) isopropylate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1903730', constants.ctx, '0')">trimethylsilylazide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8489014', constants.ctx, '0')">(-)-(4S,6S,8R)-8-(hydroxymethyl)-1,7-dioxaspiro[5.5]undecan-4-ol</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-20&deg;C;&nbsp;Ring cleavage;&nbsp;48&nbsp;h;&nbsp;&nbsp;Product distribution;&nbsp;<br /> &nbsp;