Sodium borohydride → HCID 86677832, compound

HRID 1499911Notes

Reaction equation

HRID 1499911 reaction equation
[C:1]([C:4]1[C:5]([O:24][CH3:25])=[C:6]([CH:13]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)[C:7]([C:11]#[N:12])=[C:8]([CH3:10])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C.O>[C:11]([C:7]1[C:8]([CH3:10])=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[C:5]([O:24][CH3:25])[C:6]=1[CH:13]1[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:16]1)#[N:12]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86677831Tert-butyl 3-(3-acetyl-6-cyano-2-methoxy-5-methylphenyl)azetidine-1-carboxylate

Product 1

HCID 86677832HCID 86677832, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl 3-(3-acetyl-6-cyano-2-methoxy-5-methylphenyl)azetidine-1-carboxylate (2.2 g, 6.4 mmol) was dissolved in methanol (20 mL) and cooled in ice bath. The sodium tetrahydroborate (0.26 g, 7.0 mmol) was added portionwise and the reaction was monitored by LC/MS. After stirring for 1 h the reaction was complete. This was diluted with ethyl acetate and water. The combined organic layer was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to give crude tert-butyl 3-[2-cyano-5-(1-hydroxyethyl)-6-methoxy-3-methylphenyl]azetidine-1-carboxylate as a yellow foam (2.1 g, 99%). LCMS calculated for C15H19N2O4(M+H)+: m/z=291.1; found: 291.1.

Workup

  1. temperaturecooled in ice bath
  2. washThe combined organic layer was washed with water, saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5482fb0c20b5415382dde7b996802624
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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