Acetic Acid → N-(3-Hydroxymethyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-2-(3-trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetamide

HRID 1162745Notes

Reaction equation

HRID 1162745 reaction equation
[CH:1]([C:3]1[C:4]2[CH2:28][CH2:27][CH2:26][CH2:25][C:5]=2[S:6][C:7]=1[NH:8][C:9](=[O:24])[CH2:10][N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]([C:20]([F:23])([F:22])[F:21])=[N:12]1)=[O:2].[BH4-].[Na+].C(O)(=O)C>CCO.C(OCC)C>[OH:2][CH2:1][C:3]1[C:4]2[CH2:28][CH2:27][CH2:26][CH2:25][C:5]=2[S:6][C:7]=1[NH:8][C:9](=[O:24])[CH2:10][N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]([C:20]([F:23])([F:22])[F:21])=[N:12]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 59520503N-(3-Formyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-2-(3-trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetamide

Product 1

HCID 52945134N-(3-Hydroxymethyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-2-(3-trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetamideYield 97.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

N-(3-Formyl-4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-2-(3-trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetamide (1.30 g, 3.16 mmol) was added portionwise, with stirring, to a solution of sodium borohydride (359 mg, 9.49 mmol) in EtOH (300 mL). The resulting mixture was stirred at RT for 40 min. Acetic acid was added dropwise until the effervescence ceased. The resulting mixture was concentrated in vacuo to afford an off-white solid. The solid was dissolved in diethyl ether (200 mL) and washed with water (100 mL). The organics were dried over sodium sulfate and concentrated in vacuo to yield the title compound as a yellow solid (1.27 g, 3.08 mmol, 97%).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customto afford an off-white solid
  3. washwashed with water (100 mL)
  4. dry with materialThe organics were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25c85bfc27dc4582bc8e7606d94d76e8
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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