Sodium borohydride → Benzyl 3-[3-chloro-6-ethoxy-5-(1-hydroxyethyl)-2-methylphenyl]azetidine-1-carboxylate

HRID 1499717Notes

Reaction equation

HRID 1499717 reaction equation
[C:1]([C:4]1[C:5]([O:26][CH2:27][CH3:28])=[C:6]([CH:12]2[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:13]2)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.O>[Cl:10][C:8]1[C:7]([CH3:11])=[C:6]([CH:12]2[CH2:15][N:14]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[CH2:13]2)[C:5]([O:26][CH2:27][CH3:28])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666866Benzyl 3-(3-acetyl-5-chloro-2-ethoxy-6-methylphenyl)azetidine-1-carboxylate

Product 1

HCID 86677656Benzyl 3-[3-chloro-6-ethoxy-5-(1-hydroxyethyl)-2-methylphenyl]azetidine-1-carboxylateYield 88.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of benzyl 3-(3-acetyl-5-chloro-2-ethoxy-6-methylphenyl)azetidine-1-carboxylate (0.35 g, 0.87 mmol) in methanol (5 mL) cooled at 0° C. was added sodium tetrahydroborate (0.040 g, 1.0 mmol). The mixture was stirred at room temperature for 1 hour, then diluted with water, extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated to give the crude alcohol (0.31 g, 88%). LCMS calculated for C22H27ClNO4 (M+H)+: m/z=404.2; Found: 404.0,

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-19c72ac56b584ec59cc9b2f0d12355a8
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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