2-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acetic acid → tert-Butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate

HRID 246432Notes

Reaction equation

HRID 246432 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]>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

3

Reactant 1

HCID 110959892-(1-(Tert-butoxycarbonyl)azetidin-3-yl)acetic acid

Product 1

HCID 22594530tert-Butyl 3-(2-hydroxyethyl)azetidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(1-(tert-butoxycarbonyl)azetidin-3-yl)acetic acid (529 mg, 2.46 mmol) in THF (5.29 mL) was cooled to 0° C. and treated with a borane-methyl sulfide complex 2M in THF (2.46 mL, 4.92 mmol), then slowly warmed to rt. After stirring for 18 h, the reaction mixture was quenched by drop-wise addition of 2 N NaOH (7 mL) then extracted with dichloromethane (4×30 mL). The organic layers were combined, dried (MgSO4), and concentrated to give tert-butyl 3-(2-hydroxyethyl)azetidine-1-carboxylate (495 mg, 2.46 mmol, 100%) as a colorless oil. 1H NMR (CDCl3) δ: 3.96 (t, J=8.3 Hz, 2H), 3.47-3.64 (m, 4H), 2.50-2.67 (m, 1H), 1.73-1.86 (m, 2H), 1.37 (s, 9H).

Workup

  1. customthe reaction mixture was quenched by drop-wise addition of 2 N NaOH (7 mL)
  2. extractionthen extracted with dichloromethane (4×30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ea321ad695a0497b9863a6f2c279e2b2
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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