Acetic Acid → HCID 22562204, compound

HRID 982633Notes

Reaction equation

HRID 982633 reaction equation
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[N:22]=[C:21]4[CH:29]=O)[CH2:16][CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C@H:31]12[CH2:37][C@H:34]([NH:35][CH2:36]1)[CH2:33][N:32]2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>ClCCCl>[C:1]1([C:7]2([N:14]3[CH2:15][CH2:16][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[N:22]=[C:21]4[CH2:29][N:35]4[CH2:36][CH:31]5[CH2:37][CH:34]4[CH2:33][N:32]5[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:18][CH2:19]3)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 22562206HCID 22562206, compound

Product 1

HCID 22562204HCID 22562204, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 1-[1-(1-phenylcycloheptyl)-4-piperidinyl]-1H-benzimidazole-2-carbaldehyde (this was prepared in preparation 10, 159 mg, 0.396 mmol) and t-butyl (1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (86 mg, 0.436 mmol) in 1,2-dichloroethane (4 ml) was added NaBH(OAc)3 (117 mg, 0.554 mmol) and acetic acid (48 μl, 0.832 mmol) at room temperature. After 24 hour stirring, the reaction mixture was quenched with NaHCO3 solution and extracted with CH2Cl2. The extracts combined were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (1 mm thick plate×2, acetone/n-hexane:1/3) to afford 227 mg (98%) of title compound as colorless foam.

Workup

  1. customthe reaction mixture was quenched with NaHCO3 solution
  2. extractionextracted with CH2Cl2
  3. dry with materialThe extracts combined were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (1 mm thick plate×2, acetone/n-hexane:1/3)

Sources & evidence

ORD record
ord-8866b22c6891468a87aca00dd97ea8ff
Source dataset
uspto-grants-2005_03
Patent number
US06861425B2

Reaction notes

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