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

HRID 624282Notes

Reaction equation

HRID 624282 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]>O1CCCC1>[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-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(1-(tert-butoxycarbonyl)azetidin-3-yl)acetic acid (1 g, 4.65 mmol) in tetrahydrofuran (5 ml) was cooled to 0° C. and treated with borane tetrahydrofuran complex (7.00 ml, 7 mmol) dropwise by syringe. After 1 hour at 0° C. the solution was allowed to warm to room temperature and stirred overnight and then it was quenched with 20 ml of 1M aqueous NaOH. The separated aqueous layer was extracted with ether (2×15 ml), dried with magnesium sulfate, filtered and concentrated to give the title compound which was used without purification.

Workup

  1. additiontreated with borane tetrahydrofuran complex (7.00 ml, 7 mmol) dropwise by syringe
  2. customit was quenched with 20 ml of 1M aqueous NaOH
  3. extractionThe separated aqueous layer was extracted with ether (2×15 ml)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fbf5ba5b8064b51addc6bd3b47c20e4
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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