Triphenylphosphine → HCID 67001595, compound

HRID 2191582Notes

Reaction equation

HRID 2191582 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH:8]([CH2:14][OH:15])[C:9]([CH3:13])([CH3:12])[CH2:10]O)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][CH:8]1[C:9]([CH3:13])([CH3:12])[CH2:10][O:15][CH2:14]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11776Triphenylphosphine2×HCID 73096807HCID 73096807, compound

Product 1

HCID 67001595HCID 67001595, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Hydroxy-1-hydroxymethyl-2,2-dimethyl-propyl)-carbamic acid tert-butyl ester (104 mg, 0.44 mmol) was dissolved in dichloromethane (2.2 mL). Triphenylphosphine (0.115 g, 0.44 mmol) was added followed by azodiethylcarboxylate (0.16 mL, 0.88 mmol). After 30 min additional triphenylphosphine (0.115 g, 0.44 mmol) and azodiethylcarboxylate (0.16 mL, 0.88 mmol) were added and the reaction mixture was stirred for 72 h. The solvent was evaporated and the residue purified by silica gel chromatography (ethyl acetate/hexanes) to give 70 mg (74%) of (4,4-dimethyl-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8944090ef8fe48e2bf7373bbd6eebcb2
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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