Benzaldehyde → HCID 131726740, compound

HRID 899569Notes

Reaction equation

HRID 899569 reaction equation
C([BH3-])#N.[Na+].[ClH:5].[O:6]([C:13]1([OH:24])[CH:23]=[CH:22][C:16]([C:17]([CH3:21])([CH3:20])[CH2:18][NH2:19])=[CH:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO.CCOCC>[ClH:5].[CH2:25]([NH:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]1[CH:15]=[CH:14][C:13]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([OH:24])[CH2:23][CH:22]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 131726742HCID 131726742, compound

Product 1

HCID 131726740HCID 131726740, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Sodium cyanoborohydride (10 mg, 0.17 mmol) was added to a solution of 83 (30 mg, 0.11 mmol) and benzaldehyde (12 μl, 0.12 mmol) in MeOH (2 ml). After 1 hour stirring, the reaction mixture was diluted with ether and washed with water. The aqueous was extracted with ether and then combined organic layers were washed with water, and brine, then dried over MgSO4. The crude product was purified via flash SiO2 (eluted with hexane/ethyl acetate (10:1)) to give the protected amine as a white solid. The protected amine was dissolved in 3 N HCl solution in ethylacetate (2 ml) and the reaction mixture was stirred at ambient temperature for 15 hours. The crude reaction mixture was concentrated in vacuo and dried under high vacuum pressure to give 84 as a white solid (25 mg, 61% yield). 1H-NMR (400 MHz, DMSO-d6) δ 8.83 (brd s, 2H), 7.52-7.32 (m, 10H), 7.15 (d, J=7.6 Hz, 1H), 7.02-6.95 (m, 3H), 4.09 (s, 2H), 3.34 (s, 2H), 1.35 (s, 6H).

Workup

  1. washwashed with water
  2. extractionThe aqueous was extracted with ether
  3. washcombined organic layers were washed with water, and brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified via flash SiO2 (eluted with hexane/ethyl acetate (10:1))

Sources & evidence

ORD record
ord-acee4abc6de54a2297d6a49412adddb8
Source dataset
uspto-grants-2008_04
Patent number
US07355079B2

Reaction notes

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