Tert-Butylamine → n-[6-(Tert-butylamino-methyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[5,5-dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-acetamide

HRID 747050Notes

Reaction equation

HRID 747050 reaction equation
[CH3:1][C:2]1([CH3:37])[CH2:7][N:6]([S:8]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])(=[O:10])=[O:9])[CH:5]([CH2:20][C:21]([NH:23][C@H:24]2[C:33]3[C:28](=[CH:29][C:30]([CH:34]=O)=[CH:31][CH:32]=3)[CH2:27][CH2:26][CH2:25]2)=[O:22])[C:4](=[O:36])[NH:3]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:52]([NH2:56])([CH3:55])([CH3:54])[CH3:53]>CCOC(C)=O>[C:52]([NH:56][CH2:34][C:30]1[CH:29]=[C:28]2[C:33](=[CH:32][CH:31]=1)[CH:24]([NH:23][C:21](=[O:22])[CH2:20][CH:5]1[C:4](=[O:36])[NH:3][C:2]([CH3:37])([CH3:1])[CH2:7][N:6]1[S:8]([C:11]1[C:12]([CH3:19])=[CH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])(=[O:10])=[O:9])[CH2:25][CH2:26][CH2:27]2)([CH3:55])([CH3:54])[CH3:53]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 5049666Sodium triacetoxyborohydrideHCID 1317269512-[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-n-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1(r)-yl)-acetamide

Product 1

HCID 72373799n-[6-(Tert-butylamino-methyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[5,5-dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

2-[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(R,S)-yl]-N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1(R)-yl)-acetamide (Step b, 550 mg, 1.0 mmol) was dissolved in 1,2-dicholoethane (10 mL) and tert-butylamine (1.5 mL). NaBH(OAc)3 (1.5 g, 6.0 mmol) was added to the reaction, and heated to 85° C. in a sealed tube for 18 h. The mixture was cooled to RT, diluted with EtOAc (25 mL), washed with sat. NaHCO3 solution (2×), and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 10% MeOH in CH2Cl2+1% NH3) to provide the title compound. ESMS 583.4 (M+H), 581.5 (M−H).

Workup

  1. temperatureThe mixture was cooled to RT
  2. washwashed with sat. NaHCO3 solution (2×), and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a residue which
  7. customwas purified by column chromatography (SiO2, 10% MeOH in CH2Cl2+1% NH3)

Sources & evidence

ORD record
ord-09bf9538bb3f469e8d9f6f8279135a9d
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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