Acetic Acid → HCID 57495630, compound

HRID 1092345Notes

Reaction equation

HRID 1092345 reaction equation
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][C:6]3([OH:14])[CH2:7][C:8]([OH:13])([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[C:15]([NH:22][C:23]1([CH:28]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O)(=O)C.C([O-])(O)=O.[Na+]>CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[C:18]([O:17][C:15](=[O:16])[NH:22][C:23]1([CH2:28][NH:2][CH:3]2[CH:10]3[CH2:9][C:8]4([OH:13])[CH2:7][C:6]([OH:14])([CH2:5][CH:4]2[CH2:12]4)[CH2:11]3)[CH2:24][CH2:25][CH2:26][CH2:27]1)([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 16217741tert-Butyl (1-formylcyclopentyl)carbamateHCID 57495631HCID 57495631, compound

Product 1

HCID 57495630HCID 57495630, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 5049666Sodium triacetoxyborohydrideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 6-amino-adamantane-1,3-diol hydrochloride (258 mg, J. Med. Chem. 50, 2007, 149), N-Boc-cycloleucinal (250 mg) and acetic acid (0.67 ml) in MeOH (5.0 ml), sodium triacetoxyborohydride was added at room temperature. The mixture was stirred at 60° C. for 30 min. The mixture was basified with saturated NaHCO3 solution. The mixture was extracted with AcOEt, washed with brine, dried over MgSO4 and evaporated. The residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=from 100:0:0 to 90:9:1) to obtain the title compound (250 mg, 56%) as a white amorphous.

Workup

  1. additionwas added at room temperature
  2. extractionThe mixture was extracted with AcOEt
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified with silica gel chromatography (CH2Cl2:MeOH:NH4OH=from 100:0:0 to 90:9:1)

Sources & evidence

ORD record
ord-3f6498360f464d6caefacd9f6a365a9a
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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