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Sodium triacetoxyborohydride → methyl 4-[(1S)-1-[[(3R)-2-(2-(4-fluorophenoxy)ethyl)-3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]ethyl]benzoate

HRID 2205307
Notes
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Reaction equation

HRID 2205307 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@H:4]([C:12]([NH:14][C@H:15]([C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)[CH3:16])=[O:13])[NH:3]1.[F:27][C:28]1[CH:37]=[CH:36][C:31]([O:32][CH2:33][CH:34]=O)=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:27][C:28]1[CH:37]=[CH:36][C:31]([O:32][CH2:33][CH2:34][N:3]2[C@@H:4]([C:12]([NH:14][C@H:15]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:25][CH:26]=3)[CH3:16])=[O:13])[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:2]2)=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 110518692-(4-Fluorophenoxy)acetaldehydeHCID 118876958methyl 4-[(1S)-1-[[(3R)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]amino]ethyl]benzoate hydrochloride

Product 1

HCID 118876972methyl 4-[(1S)-1-[[(3R)-2-(2-(4-fluorophenoxy)ethyl)-3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]ethyl]benzoateYield 54.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of methyl 4-[(1S)-1-[[(3R)-1,2,3,4-tetrahydroisoquinoline-3-carbonyl]amino]ethyl]benzoate hydrochloride (800 mg, 2.13 mmol) and 2-(4-fluorophenoxy)acetaldehyde (493 mg, 3.2 mmol) in 1,2-dichloroethane (10.7 mL), add sodium triacetoxyborohydride (633 mg, 2.99 mmol) and stir the mixture at room temperature overnight. Add saturated aqueous NaHCO3 (25 mL), and extract the aqueous layer with ethyl acetate (2×25 mL). Wash the combined organic layers with saturated aqueous NaCl (25 mL), dry the organic phase over MgSO4, filter, and concentrate the filtrate under reduced pressure. Subject the resulting crude material to flash chromatography on silica gel using a 0% to 60% EtOAc/hexanes gradient. Consolidate the fractions containing the product, and concentrate them under reduced pressure to furnish the title compound as a colorless foam (550 mg, 54% yield). Mass spectrum (m/z): 477 ([M+H]+).

Workup

  1. extractionAdd saturated aqueous NaHCO3 (25 mL), and extract the aqueous layer with ethyl acetate (2×25 mL)
  2. washWash the combined organic layers with saturated aqueous NaCl (25 mL)
  3. dry with materialdry the organic phase over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate the filtrate under reduced pressure
  6. additioncontaining the product
  7. concentrationconcentrate them under reduced pressure

Sources & evidence

ORD record
ord-8f27544b20bb4e3d952c6d338656317e
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371289B2

Reaction notes

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