Sodium triacetoxyborohydride → HCID 16048762, compound

HRID 1364149Notes

Reaction equation

HRID 1364149 reaction equation
[N:1]1[N:2]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])=[CH:13][CH:12]=2)[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=12.[CH:23]1([CH2:26]C=O)[CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:23]1([CH2:26][N:8]2[CH2:9][CH2:10][C:4]3=[CH:3][N:2]([C:11]4[CH:12]=[CH:13][C:14]([N:17]5[CH2:21][CH2:20][CH2:19][C:18]5=[O:22])=[CH:15][CH:16]=4)[N:1]=[C:5]3[CH2:6][CH2:7]2)[CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 103078492-CyclopropylacetaldehydeHCID 66930837HCID 66930837, compound

Product 1

HCID 16048762HCID 16048762, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)phenyl]-2-pyrrolidinone (may be prepared as described in Description 22) (55 mg, 0.10 mmol) in dichloromethane (5 ml) was added cyclopropylacetaldehyde (26 mg, 0.30 mmol) and acetic acid (3 drops). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added and stirring continued for 18 hours. The resulting crude mixture was diluted with methanol and then purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were collected and solvent evaporated in vacuo. Crude product was triturated with ethyl acetate to afford the title compound (E19). MS (ES+) m/e 351 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. custompurified by SCX
  4. washeluting with methanol
  5. customThe basic fractions were collected
  6. customsolvent evaporated in vacuo
  7. customCrude product was triturated with ethyl acetate

Sources & evidence

ORD record
ord-94089ebcb271446fa853f5b607bd67c8
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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