Sodium borohydride → Tert-butyl 1-(2-(4-cyanophenyl)-2-hydroxyethyl)azetidine-3-carboxylate

HRID 1948505Notes

Reaction equation

HRID 1948505 reaction equation
Br.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:23])[CH2:11][N:12]2[CH2:15][CH:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)=[CH:6][CH:5]=1)#[N:3].[BH4-].[Na+]>CO>[C:2]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:23])[CH2:11][N:12]2[CH2:13][CH:14]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:15]2)=[CH:8][CH:9]=1)#[N:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131730340HCID 131730340, compound

Product 1

HCID 66955243Tert-butyl 1-(2-(4-cyanophenyl)-2-hydroxyethyl)azetidine-3-carboxylateYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl 1-(2-(4-cyanophenyl)-2-oxoethyl)azetidine-3-carboxylate, hydrobromide (170 mg, 0.446 mmol) in MeOH (5 mL) was added sodium borohydride (25 mg, 0.661 mmol). The reaction mixture was stirred for 1 hour. The reaction was quenched with water. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried with MgSO4, filtered, and concentrated to yield 100 mg of tert-butyl 1-(2-(4-cyanophenyl)-2-hydroxyethyl)azetidine-3-carboxylate. MS (m+1)=303. HPLC Peak RT=0.90 minutes (Analytical Method B).

Workup

  1. customThe reaction was quenched with water
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed with H2O
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-867c63d8d8f74c999d86d80ca54a9aa9
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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