Triethylamine → HCID 70154690, compound

HRID 2301175Notes

Reaction equation

HRID 2301175 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:4]1)=O.Cl.Cl.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([N:39]([CH:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)[CH2:40][CH:41]=[CH2:42])[CH:34]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C>ClCCCl.CCOC(C)=O>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][C@H:14]1[N:5]1[CH2:6][C@H:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@@H:3]([CH2:1][N:46]2[CH2:47][CH2:48][CH:43]([N:39]([CH2:40][CH:41]=[CH2:42])[C:35]3[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=3)[CH2:44][CH2:45]2)[CH2:4]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 18374717HCID 18374717, compoundHCID 86758721HCID 86758721, compound

Product 1

HCID 70154690HCID 70154690, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)cyclohexaneacetic acid, benzyl ester (35 mg, 0.086 mmol; prepared above as Aldehyde 4), 4-(N-(pyrid-3-yl)-N-allylamino)piperidine dihydrochloride (28 mg, 0.103 mmol, from Step B), sodium triacetoxyborohydride (44 mg, 0.206 mmol) and triethylamine (0.03 mL, 0.206 mmol) were stirred in 2 mL 1,2-dichloroethane for 12 h. The mixture was diluted with 25 mL EtOAc and washed with water and sat'd aq. NaCl. The organic phase was dried over Na2SO4 and concentrated. Flash chromatography (5 grams silica, 0→2% MeOH/CH2Cl2 eluent) afforded 37 mg (70%) of the title compound. M/z; (M+H)=607.4 (obs), 607.4 (calc.).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b7e906d2a1644d5cabec4c994119aa05
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

Loading…