Diethyl Ether → Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate

HRID 265907Notes

Reaction equation

HRID 265907 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][C:13](OCC)=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[BH4-].CC[O:22]CC>>[C:1]([N:8]1[CH2:11][CH:10]([CH:12]([OH:22])[CH3:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 4148881Lithium borohydrideHCID 15256325Tert-butyl 3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate

Product 1

HCID 58348207Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate

Conditions

Temperature
55 °C

Procedure

A stirred solution of 33-4 (0.96 g, 3.9 mmol) in ether (20 mL) at ambient temperature was treated with LiBH4 (0.34 g, 15.8 mmol) then heated to 55° C. After 45 min the cooled reaction was quenched with 5% KHSO4 (10 mL) and then diluted with EtOAc. The organic phase was washed with 5% KHSO4 and brine, dried (MgSO4), and concentrated to give 33-5 (0.79 g) as a colorless oil. Rf 0.46 (silica, EtOAc).

Workup

  1. customAfter 45 min the cooled reaction
  2. customwas quenched with 5% KHSO4 (10 mL)
  3. additiondiluted with EtOAc
  4. washThe organic phase was washed with 5% KHSO4 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ef28c0fd91c4258a636a83308720e66
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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