Lithium borohydride → tert-Butyl 3-(hydroxymethyl)-3-methylazetidine-1-carboxylate

HRID 237492Notes

Reaction equation

HRID 237492 reaction equation
C[O:2][C:3]([C:5]1([CH3:16])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1)=O.[BH4-].[Li+]>O1CCCC1.O>[C:12]([O:11][C:9]([N:7]1[CH2:8][C:5]([CH2:3][OH:2])([CH3:16])[CH2:6]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 574158901-Tert-butyl 3-methyl 3-methylazetidine-1,3-dicarboxylate

Product 1

HCID 70700778tert-Butyl 3-(hydroxymethyl)-3-methylazetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Methyl-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (WO2006/73361 A1, 2006) (1.1 g) is dissolved in 20 mL of tetrahydrofurane. Lithiumborohydride (16.8 mL of a 2 M solution in tetrahydrofurane) is added dropwise and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with water, washed with a saturated ammonium chloride water solution and the organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50:50) to give the title compound. Yield: 970 mg.

Workup

  1. washwashed with a saturated ammonium chloride water solution
  2. customthe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue is chromatographed on silica gel (hexane/ethyl acetate 100:0→50:50)

Sources & evidence

ORD record
ord-a0d3ea4ab57740ebbd2ab55fa4e4a52b
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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