Sodium borohydride → Tert-butyl 3-(3-chloro-2-fluoro-5-(1-hydroxyethyl)-6-methoxyphenyl)azetidine-1-carboxylate

HRID 1499687Notes

Reaction equation

HRID 1499687 reaction equation
[C:1]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[C:7]([F:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:10][C:8]1[C:7]([F:11])=[C:6]([CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15]2)[C:5]([O:23][CH3:24])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666859tert-Butyl 3-(3-acetyl-5-chloro-6-fluoro-2-methoxyphenyl)azetidine-1-carboxylate

Product 1

HCID 86666860Tert-butyl 3-(3-chloro-2-fluoro-5-(1-hydroxyethyl)-6-methoxyphenyl)azetidine-1-carboxylateYield 110%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-(3-acetyl-5-chloro-6-fluoro-2-methoxyphenyl)azetidine-1-carboxylate (0.17 g, 0.48 mmol) in methanol (3 mL) cooled at 0° C. was added sodium tetrahydroborate (0.022 g, 0.57 mmol). The mixture was stirred at room temperature for 1 hour, then quenched with water, extracted with EtOAc. The organic layers were combined, dried over MgSO4 and concentrated to give the crude alcohol (0.19 g). LCMS calculated for C17H23ClFNO4Na (M+Na)+: m/z=382.1; Found: 382.0.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-302325ef90b94a30b80d72ff8f9803e2
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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