Triethylamine → HCID 86690379, compound

HRID 513890

Reaction equation

HRID 513890 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH:4]=O.[Cl:7][C:8]1[CH:49]=[CH:48][C:11]([CH2:12][NH:13][CH2:14][C:15]([C@:17]23[CH2:43][C:42](=[O:44])[C:41]([CH:45]([CH3:47])[CH3:46])=[C:18]2[C@@H:19]2[C@@:32]([CH3:35])([CH2:33][CH2:34]3)[C@@:31]3([CH3:36])[C@@H:22]([C@:23]4([CH3:40])[C@@H:28]([CH2:29][CH2:30]3)[C:27]([CH3:38])([CH3:37])[C@@H:26]([OH:39])[CH2:25][CH2:24]4)[CH2:21][CH2:20]2)=[O:16])=[CH:10][CH:9]=1.CCN(CC)CC.C([BH3-])#N.[Na+]>CO.ClCCCl.O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][N:13]([CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[CH2:14][C:15]([C@:17]23[CH2:43][C:42](=[O:44])[C:41]([CH:45]([CH3:46])[CH3:47])=[C:18]2[C@@H:19]2[C@@:32]([CH3:35])([CH2:33][CH2:34]3)[C@@:31]3([CH3:36])[C@@H:22]([C@:23]4([CH3:40])[C@@H:28]([CH2:29][CH2:30]3)[C:27]([CH3:37])([CH3:38])[C@@H:26]([OH:39])[CH2:25][CH2:24]4)[CH2:21][CH2:20]2)=[O:16])=[CH:48][CH:49]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 101976222-(Dimethylamino)acetaldehydeHCID 68267104HCID 68267104, compound

Product 1

HCID 86690379HCID 86690379, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(dimethylamino)acetaldehyde (4.79 g, 38.8 mmol) in methanol (50 ml) and 1,2-dichloroethane (DCE) (25 ml) was added (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-(4-chlorobenzylamino)acetyl)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a,4,5,5a,6,7,7a,8,9,10,11,11a,11b,12,13,13a-hexadecahydro-3H-cyclopenta[a]chrysen-2(5bH)-one (15) (5 g, 7.75 mmol) at 000° C. The pH was adjusted to 7 with Et3N. The reaction mixture was stirred at rt for 1 h. Sodium cyanoborohydride (0.487 g, 7.75 mmol) was added and the mixture was stirred overnight. The reaction was diluted with water (40 ml), and extracted with DCM (60 ml×3). The combined organic layer was washed with brine (20 ml), dried over sodium sulfate and filtered to afford crude product (3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-(2-((4-chlorobenzyl)(2-(dimethylamino)ethyl)amino)acetyl)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a,4,5,5a,6,7,7a,8,9,10,11,11a,11b,12,13,13a-hexadecahydro-3H-cyclopenta[a]chrysen-2(5bH)-one (52) (5 g, 5.89 mmol, 76% yield) as a light yellow solid, which was used in the next step. LC/MS: m/z calculated 678.5. found 679.3 (M+1)+.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionextracted with DCM (60 ml×3)
  3. washThe combined organic layer was washed with brine (20 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7a4037d8833e4367887d15ccc87164c3
Source dataset
uspto-grants-2015_08
Patent number
US09102685B2

Linked notes

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