Triphenylphosphine → (r)-1-(Benzyloxy)-3-(cyclopentylmethyl)azetidin-2-one

HRID 1366372Notes

Reaction equation

[CH:1]1([CH2:6][C@H:7]([CH2:19][OH:20])[C:8]([NH:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:1]1([CH2:6][C@@H:7]2[CH2:8][N:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]2=[O:20])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of (2R)-3-cyclopentyl-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]propanamide (22.5 g, 81 mmol) and triphenylphosphine (22.5 g, 97 mmol) in THF (800 mL) at 0° C. was added dropwise diisopropyl azodicarboxylate (18.9 mL, 97 mmol). The reaction mixture was maintained at 0° C. for 45 min and was then evaporated. Purification by chromatography on silica gel using an eluting system of hexane/EtOAc (95:5) provided (3R)-3-(cyclopentylmethyl)-1-[(phenylmethyl)oxy]-2-azetidinone (16.9 g, 81%). LCMS: (M+H)+: 260.1.

Workup

customwas then evaporated
customPurification by chromatography on silica gel using an eluting system of hexane/EtOAc (95:5)

Sources & evidence

ORD record: ord-ba60cc7b25ae4b8dba3f754a99ddf88a
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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