Sodium borohydride → Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate

HRID 1873854Notes

Reaction equation

HRID 1873854 reaction equation
[C:1]([CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59841137tert-Butyl 3-acetylazetidine-1-carboxylate

Product 1

HCID 58348207Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylateYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 100 ml round bottom flask was added tert-butyl 3-acetylazetidine-1-carboxylate (2.06, 10.3 mmol) and 30 ml MeOH. NaBH4 (0.403 g, 10.6 mmol) was added in portions. The resulting reaction mixture was stirred at room temperature for 15 minutes. The volatiles were removed under vacuum. The residue was treated with 50 ml 10% KOH and extracted with 2×50 ml ethyl acetate. The organics were combined and dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel column eluted with 1:4 to 1:2 E/H to give 2.06 g desired product as colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe volatiles were removed under vacuum
  3. additionThe residue was treated with 50 ml 10% KOH
  4. extractionextracted with 2×50 ml ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel column
  9. washeluted with 1:4 to 1:2 E/H

Sources & evidence

ORD record
ord-d39f5412c0c44f919b33dddfb2ee1318
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

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