Sodium cyanoborohydride → HCID 86690381, compound

HRID 513892Notes

Reaction equation

HRID 513892 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH:5]=O.[C:8]([O:11][C@@H:12]([C@:23]12[CH2:58][C:57](=[O:59])[C:56]([CH:60]([CH3:62])[CH3:61])=[C:24]1[C@@H:25]1[C@@:38]([CH3:41])([CH2:39][CH2:40]2)[C@@:37]2([CH3:42])[C@@H:28]([C@:29]3([CH3:55])[C@@H:34]([CH2:35][CH2:36]2)[C:33]([CH3:44])([CH3:43])[C@@H:32]([O:45][C:46](=[O:54])[CH2:47][C:48]([CH3:53])([CH3:52])[C:49]([OH:51])=[O:50])[CH2:31][CH2:30]3)[CH2:27][CH2:26]1)[CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)(=[O:10])[CH3:9].C([BH3-])#N.[Na+]>CO>[C:8]([O:11][C@@H:12]([C@:23]12[CH2:58][C:57](=[O:59])[C:56]([CH:60]([CH3:62])[CH3:61])=[C:24]1[C@@H:25]1[C@@:38]([CH3:41])([CH2:39][CH2:40]2)[C@@:37]2([CH3:42])[C@@H:28]([C@:29]3([CH3:55])[C@@H:34]([CH2:35][CH2:36]2)[C:33]([CH3:44])([CH3:43])[C@@H:32]([O:45][C:46](=[O:54])[CH2:47][C:48]([CH3:52])([CH3:53])[C:49]([OH:51])=[O:50])[CH2:31][CH2:30]3)[CH2:27][CH2:26]1)[CH2:13][N:14]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[CH2:5][CH2:4][N:3]([CH3:7])[CH3:2])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 13908802(Dimethylamino)acetaldehyde--hydrogen chloride (1/1)HCID 86690382HCID 86690382, compound

Product 1

HCID 86690381HCID 86690381, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(dimethylamino)acetaldehyde, hydrochloride (238 mg, 1.922 mmol) in methanol (12 mL) was added 4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((S)-1-acetoxy-2-((4-chlorobenzyl)amino)ethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid (50) (150 mg, 0.192 mmol). The reaction mixture was stirred at rt for 2 h then sodium cyanoborohydride (121 mg, 1.922 mmol) was added and the mixture was stirred overnight. Upon completion, the mixture was purified preparative-HPLC to provide the title compound (50 mg, 24%). 1H NMR (400 MHz, CHLOROFORM-d) δ=7.35-7.12 (m, 4H), 5.65 (d, J=9.3 Hz, 1H), 4.49 (dd, J=5.8, 10.0 Hz, 1H), 3.83 (d, J=13.6 Hz, 1H), 3.55 (d, J=13.6 Hz, 1H), 3.25-2.91 (m, 7H), 2.91-2.73 (m, 7H), 2.73-2.52 (m, 3H), 2.33 (d, J=18.1 Hz, 1H), 1.99-0.72 (m, 48H); LC/MS: m/z calculated 850.5. found 851.4 (M+1)+.

Workup

  1. stirringthe mixture was stirred overnight
  2. customUpon completion, the mixture was purified preparative-HPLC

Sources & evidence

ORD record
ord-bd40fcec4baf4627b91c9a7d374e3458
Source dataset
uspto-grants-2015_08
Patent number
US09102685B2

Reaction notes

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