1-Boc-Azetidine-3-carboxylic acid → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

HRID 1091296Notes

Reaction equation

HRID 1091296 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12](O)=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylateYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran (100 mL) solution of 1-(tert-butoxycarbonyl)-3-azetidinecarboxylic acid (2.0 g, 9.94 mmol), 10M-borane-dimethyl sulfide complex (2.98 mL, 29.8 mmol) was added at room temperature, and the mixture was stirred for 14 hours. The reaction liquor was poured onto ice water (100 mL), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40S, 2% methanol/ethyl acetate), to obtain the title compound (1.83 g, 98%) as an oily matter.

Workup

  1. additionThe reaction liquor was poured onto ice water (100 mL)
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40S, 2% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-71d545bb344a45bb9900833a5a944be3
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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