Sodium cyanoborohydride → Tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate

HRID 1867329Notes

Reaction equation

HRID 1867329 reaction equation
C([BH3-])#N.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([OH:19])([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15].[CH3:20][C:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:25])[CH2:22][CH:23]=O>CO.CC(O)=O.CCOC(C)=O>[OH:19][C:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[NH:5][CH2:23][CH2:22][C:21]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:25])[CH3:20])([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 11788901tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamateHCID 210728384-(2-Aminophenyl)heptan-4-ol

Product 1

HCID 86600980Tert-butyl {3-[2-(1-hydroxy-1-propylbutyl)phenylamino]-1,1-dimethylpropyl}carbamate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.40 g (22.27 mmol) of sodium cyanoborohydride is added to a solution of 3.10 g (14.05 mmol) of 4-(2-aminophenyl)heptan-4-ol and 3.60 g (17.88 mmol) of tert-butyl (1,1-dimethyl-3-oxopropyl)carbamate in MeOH (40 mL) and AcOH (6 mL). The mixture is stirred for 16 hours at RT, diluted with EtOAc, and washed with 0.5 M aqueous KHSO4 and saturated aqueous NaCl, dried with sodium sulfate, and evaporated down in vacuo. The crude product is used in the next reaction step without any further purification. Yield: 6.00 g (quantitative yield).

Workup

  1. washwashed with 0.5 M aqueous KHSO4 and saturated aqueous NaCl
  2. dry with materialdried with sodium sulfate
  3. customevaporated down in vacuo
  4. customThe crude product is used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-b7583657aefb4139b6ff362811635af5
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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