Sodium triacetoxyborohydride → HCID 86614261, compound

HRID 2099357Notes

Reaction equation

HRID 2099357 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C@H:7]([C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])[CH2:15]3)=[O:10])[NH2:8])=[CH:4][CH:3]=1.[CH:35]([C@@H:37]1[CH2:41][C@@H:40]([OH:42])[CH2:39][N:38]1[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([NH:8][CH2:35][C@@H:37]2[CH2:41][C@@H:40]([OH:42])[CH2:39][N:38]2[C:43]([O:45][C:46]([CH3:47])([CH3:49])[CH3:48])=[O:44])[C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[C:20]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[O:21])[CH2:15]3)=[O:10])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 57219732HCID 57219732, compoundHCID 68829063HCID 68829063, compound

Product 1

HCID 86614261HCID 86614261, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.24 g of the N-[8-(4-chloro-D-phenylalanyl)-8-azabicyclo[3.2.1]oct-3-yl]-N-cyclohexyl-N′,N′-diethylurea endo compound, obtained in step 1.5, is dissolved in 3 ml of dichloromethane under N2 in the presence of 0.16 g of tert-butyl (2S,4R)-2-formyl-4-hydroxypyrrolidine-1-carboxylate and of 0.233 g of sodium triacetoxyborohydride. The reaction medium is stirred at ambient temperature for 16 h. After evaporation to dryness, 1 ml of methanol and 4 g of Dowex® 50X2 resin are added. The mixture is stirred for 1 h 30 min. After filtration and washing of the resin with tetrahydrofuran and methanol, the expected compound is released by adding a 1N solution of aqueous ammonia in methanol. The methanol is evaporated off, to give 0.28 g of tert-butyl (2S,4R)-2-({[(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]-amino}-8-azabicyclo[3.2.1]oct-8-yl)-2-oxoethyl]amino}-methyl)-4-hydroxypyrrolidine-1-carboxylate.

Workup

  1. customobtained in step 1.5
  2. customAfter evaporation to dryness, 1 ml of methanol and 4 g of Dowex® 50X2 resin
  3. additionare added
  4. stirringThe mixture is stirred for 1 h 30 min
  5. filtrationAfter filtration
  6. washwashing of the resin with tetrahydrofuran and methanol
  7. additionby adding a 1N solution of aqueous ammonia in methanol
  8. customThe methanol is evaporated off

Sources & evidence

ORD record
ord-28504243a3c34593ad6e837cb2c41b48
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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