Formaldehyde → N-(2-Methyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester

HRID 1289482Notes

Reaction equation

HRID 1289482 reaction equation
C=O.[CH2:3]([O:5][C:6](=[O:31])[C@H:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][NH:18][CH2:19]2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH3:4].[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:3]([O:5][C:6](=[O:31])[C@H:7]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][N:18]([CH3:32])[CH2:19]2)=[CH:14][CH:13]=1)(=[O:10])=[O:11])[CH3:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 54386742N-(1,2,3,4-Tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester

Product 1

HCID 54437185N-(2-Methyl-1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl esterYield 315.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aqueous formaldehyde solution (370 w/v, 3.15 ml, 42 mmol) was added to a stirred solution of N-(1,2,3,4-tetrahydroisoquinoline-7-sulphonyl)-3-cyano-(S)-phenylalanine ethyl ester (Preparation 23; 3.5 g, 8.5 mmol) in dichloromethane (100 ml). After 1 hour, sodium triacetoxyborohydride (566 mg, 2.67 mmol) was added and stirring continued for 2 hours. The reaction mixture was then washed with saturated aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated under reduced pressure to furnish the title compound (3.6 g) as a white foam. Rf 0.83 (SS 3). m/e 428 (M+H)+.

Workup

  1. waitcontinued for 2 hours
  2. washThe reaction mixture was then washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cdd67a93fbb54944933882cd4f226663
Source dataset
uspto-grants-1998_05
Patent number
US05750520

Reaction notes

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