Water → HCID 86724269, compound

HRID 594874Notes

Reaction equation

HRID 594874 reaction equation
[Li+].[BH4-].[Br:3][C:4]1[CH:5]=[C:6]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][C:8]1([CH2:10][CH2:9]1)[C:7]2([C:23]([F:30])([F:29])[C:24](OCC)=[O:25])[NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18].O>C1COCC1.[Cl-].[Na+].O>[Br:3][C:4]1[CH:5]=[C:6]2[C:13](=[CH:14][CH:15]=1)[O:12][CH2:11][C:8]1([CH2:10][CH2:9]1)[C:7]2([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[C:23]([F:29])([F:30])[CH2:24][OH:25]

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 86724272HCID 86724272, compound

Product 1

HCID 86724269HCID 86724269, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Under ice cooling, to a solution of LiBH4 (458 mg, 21.0 mmol) in THF (30 mL) was added a solution of ethyl {6-bromo-4-[(tert-butylsulfinyl)amino]-4H-spiro[chromene-3,1′-cyclopropan]-4-yl}(difluoro)acetate (5.05 g, 10.5 mmol) in THF (20 mL), and the mixture was stirred for 15 minutes at same temperature and stirred for 2 hours at room temperature. After adding H2O and brine, the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to obtain crude N-[6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-4H-spiro[chromene-3,1′-cyclopropan]-4-yl]-2-methylpropane-2-sulfinamide. The desired compound (4.6 g) was applied to the next step without further purification.

Workup

  1. stirringstirred for 2 hours at room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f9002ca5c5b343fea2af4ac4c96f19b9
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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