Formaldehyde → HCID 68467538, compound

HRID 7678Notes

Reaction equation

HRID 7678 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][CH:18]([CH3:20])[CH3:19])[CH2:13][C@H:12]1[CH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[BH3-][C:36]#N.[Na+]>CO.O>[CH2:1]([O:8][C:9](=[O:32])[NH:10][C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([CH:18]([CH3:20])[CH3:19])[CH3:36])[CH2:13][C@H:12]1[CH2:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68468186HCID 68468186, compound

Product 1

HCID 68467538HCID 68467538, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The above derivative (118ba) (1.96 g) was dissolved in MeOH (15 ml) prior to the addition of 37% formaldehyde in water (1.41 ml). After 10 min, NaBH3CN (708 mg) was added. After 2 h, the reaction was concentrated. EtOAc was added and the organic layer was washed with H2O, brine, dried, filtered, and concentrated to give [(1S,2R,4R)-2-(4-Bromo-benzenesulfonylmethyl)-4-(isopropyl-methyl-amino)-cyclohexyl]-carbamic acid benzyl ester (1.9 g), MS found: (M+H)+=539.3.

Workup

  1. waitAfter 2 h
  2. concentrationthe reaction was concentrated
  3. additionEtOAc was added
  4. washthe organic layer was washed with H2O, brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1fdf84e631d54fe4b2045e44440bcbc0
Source dataset
uspto-grants-2006_08
Patent number
US07087604B2

Reaction notes

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