Acetaldehyde → HCID 69410551, compound

HRID 1592774Notes

Reaction equation

HRID 1592774 reaction equation
[CH3:1][O:2][CH2:3][CH:4]=O.[C:6]([O:10][C:11]([N:13]1[CH:22]([CH2:23][NH:24][CH:25]([C:34]([O:36][CH3:37])=[O:35])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)C>C(#N)C>[C:6]([O:10][C:11]([N:13]1[CH:22]([CH2:23][N:24]([CH:25]([C:34]([O:36][CH3:37])=[O:35])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:4][CH2:3][O:2][CH3:1])[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)=[O:12])([CH3:8])([CH3:9])[CH3:7]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 91563MethoxyacetaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 69219311HCID 69219311, compound

Product 1

HCID 69410551HCID 69410551, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of methoxyacetaldehyde (0.15 gm, 2.03 mmol), 3-{[2-(4-Chloro-phenyl)-1-methoxycarbonyl-ethylamino]-methyl}-3,4dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester from preparation 3BC Step C (0.31 gm, 0.68 mmol) in acetonitrile was added sodium triacetoxyborohydride (0.72 gm, 3.38 mmol). After stirring overnight under a nitrogen atmosphere at r.t., additional acetaldehyde (0.25 gm) dissolved in acetonitrile and sodium triacetoxyborohydride (0.21 gm) was added, and the mixture was stirred for about 8.5 hours. The mixture was quenched at r.t. with 5N NaOH (5 mL). The aqueous phase was separated from the organic and extracted with ethyl acetate (4×). The combined organics were washed with a brine solution, and then dried, filtered and concentrated. Chromatography (gradient of ethyl acetate in hexane, 0 to 12%) gives about 0.23 g of 3-{[[2-(4-Chloro-phenyl)-1-methoxycarbonyl-ethyl]-(2-methoxy-ethyl)-amino]-methyl}-3,4dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester as a yellow oil (70%). MS (m/z, ES+): 517.2.

Workup

  1. stirringthe mixture was stirred for about 8.5 hours
  2. customThe mixture was quenched at r.t. with 5N NaOH (5 mL)
  3. customThe aqueous phase was separated from the organic and
  4. extractionextracted with ethyl acetate (4×)
  5. washThe combined organics were washed with a brine solution
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9443a3789a3e42649a131e35d42092bc
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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