Tert-Butylamine → HCID 69286066, compound

HRID 2225219Notes

Reaction equation

HRID 2225219 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH:9]1[CH2:15][CH2:14][C:12](=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17].[BH4-].[Na+].[OH-].[Na+]>[Ti+4].C(Cl)Cl.CO>[C:2]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:15][CH2:14][CH:12]([NH:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:1]

Participants

8

Reactant 4

HCID 6385Tert-ButylamineHCID 14798Sodium HydroxideHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 4311764Sodium borohydride

Product 1

HCID 69286066HCID 69286066, compoundYield 100.7%

Reagents, catalysts & solvents 3

HCID 114942Titanium cation (4+)CatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-4-BOC-aminocyclohexanone (5.00 g, 23 mmol, 1 eq.), tert-butylamine (2.46 mL, 23 mmol, 1 eq.), and titanium (IV) isoproproxide (6.87 mL, 23 mmol, 1 eq.), were mixed and stirred at RT under nitrogen overnight. MeOH (50 mL) was added followed by NaBH4 pellets (0.89 g, 23 mmol, 1 eq.). After 30 minutes added 50 mL of 1 N NaOH. Methylene chloride was added, the insoluble matter filtered, and the layers separated. The aqueous layer was extracted twice more with methylene chloride. The organic layers were combined, dried and stripped to yield (4-tert-Butylamino-cyclohexyl)-carbamic acid tert-butyl ester (6.26 g) as an amber oil, which solidified upon standing. MS found: (M+H)+=271.

Workup

  1. additionwere mixed
  2. filtrationthe insoluble matter filtered
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted twice more with methylene chloride
  5. customdried

Sources & evidence

ORD record
ord-fabf9adfddfa4042bd83d76735c97ec8
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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