Water → tert-Butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate

HRID 517979Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][C:13](O)=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B#B.O>C1COCC1>[OH:14][CH2:13][CH2:12][CH:10]1[CH2:11][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(1-(tert-Butoxycarbonyl)azetidin-3-yl)acetic acid (3.91 g) was dissolved in THF (18.17 ml) and cooled to 0° C. Diborane (1M in THF, 54.5 ml) was added dropwise and the reaction stirred for one hour. Water was added dropwise to quench unreacted borane and the mixture diluted with EtOAc (150 mL) and washed with water (100 mL). Organics were dried over sodium sulphate and solvent evaporated under reduced pressure to afford tert-butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate (100% yield) as a clear oil.

Workup

customto quench unreacted borane
additionthe mixture diluted with EtOAc (150 mL)
washwashed with water (100 mL)
dry with materialOrganics were dried over sodium sulphate and solvent
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-06fdfbde5d754866b757344ea8fa4ef1
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115126B2

Reaction notes

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