Water → HCID 131723681, compound

HRID 2298063Notes

Reaction equation

HRID 2298063 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33](C)(C)[CH3:34])=O)[CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl.ClCCl>[C:33]([O:23][CH2:22][CH3:19])(=[O:32])[CH3:34].[CH3:20][CH2:21][CH2:2][CH:3]([CH3:18])[CH3:4].[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:24][CH:25]2[CH2:26][CH2:30][NH:27][CH2:28][CH2:29]2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:15][CH:14]3[CH2:16][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:17]1)[CH2:9]2)=[O:5]

Participants

8

Reactant 4

HCID 962WaterHCID 27563701-Boc-3-aminopyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 120853462-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 2

HCID 21882781Isohexane ethyl acetateHCID 131723681HCID 131723681, compoundYield 119.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.270 g, Example 31a) and 3-amino-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester (0.325 g, Journal of Medicinal Chemistry, 1998, 41(22), 4273-4278) were dissolved in 1,2-dichloroethane (30 ml), under a nitrogen atmosphere. Sodium triacetoxyborohydride (0.24 g) was added and the mixture was stirred for 14 h at room temperature. Water and dichloromethane were added and the layers were partitioned. The organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC eluting with a gradient of 0-10% of ethanol in dichloromethane, then by chromatography over silica gel eluting with ethyl acetate: iso-hexane (1:1) then ethyl acetate: ethanol (98:2) to give the subtitle compound as a colourless oil (0.158 g).

Workup

  1. customthe layers were partitioned
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by HPLC
  6. washeluting with a gradient of 0-10% of ethanol in dichloromethane

Sources & evidence

ORD record
ord-0a5c92a876424d24bc1ec9afe4e66565
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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