Formaldehyde → HCID 25053963, compound

HRID 2423160Notes

Reaction equation

HRID 2423160 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][C@H:16]1[NH:38][CH2:37][C:20]2=[C:21]3[C:25](=[CH:26][CH:27]=[C:19]2[O:18][CH2:17]1)[N:24]([S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH:23]=[CH:22]3.C=O>C1COCC1>[CH3:1][N:38]1[CH2:37][C:20]2=[C:21]3[C:25](=[CH:26][CH:27]=[C:19]2[O:18][CH2:17][C@H:16]1[CH3:15])[N:24]([S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:29])=[O:30])[CH:23]=[CH:22]3

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 25053962HCID 25053962, compound

Product 1

HCID 25053963HCID 25053963, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (7.5 mg, 0.040 mmol) was added to a solution of (3R)-3-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Example 73, 0.010 g, 0.029 mmol) and formaldehyde (37 wt. % in H2O, 0.020 mL, 0.25 mmol) in THF (1 mL). The mixture was stirred for 20 minutes, evaporated and the crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN) to give the title compound as a white solid (4 mg) in the form of the trifluoroacetate salt. MS m/z 357 [M+H]+.

Workup

  1. customevaporated
  2. customthe crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN)

Sources & evidence

ORD record
ord-e6cfe85db079457aa9647041beda594c
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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