Acetone → HCID 178457354, compound

HRID 2225217Notes

Reaction equation

HRID 2225217 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]([CH3:19])=O.[C:20](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].C=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([N:14]([CH:17]([CH3:19])[CH3:16])[CH3:20])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 180AcetoneHCID 712FormaldehydeHCID 14798Sodium Hydroxide2×HCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 178457354HCID 178457354, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 1 h, Step 1: A sample of (4-Amino-cyclohexyl)-carbamic acid tert-butyl ester (available from Albany Molecular Research; 2.00 g, 10.7 mmol, 1 eq.), acetone (1.18 mL, 16.1 mmol, 1.5 eq.), sodium triacetoxyborohydride (3.41 g, 16.1 mmol, 1.5 eq.) and 50 mL of methylene chloride were stirred at RT for 20 hours. Added 20 mL of 1 N NaOH and stirred 10 minutes then extracted 3× with methylene chloride. The organic layers were combined, dried and stripped in vacuo to obtain an oil. Added sodium triacetoxyborohydride (3.41 g, 16.1 mmol, 1.5 eq.) and 37% formaldehyde (aqueous) (2.62 mL, 32.2 mmol, 3 eq). Stirred 4 hours. Added 20 mL of 1 N NaOH and stirred 10 minutes then extracted the aqueous 3× with methylene chloride. The organic layers were combined, dried and stripped in vacuo to give cis-[4-(Isopropyl-methyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester (3.20 g) as a colorless oil. MS found: (M+H)+=271.

Workup

  1. customExample 1 h, Step 1
  2. customwere stirred at RT for 20 hours
  3. extractionthen extracted 3× with methylene chloride
  4. customdried
  5. customto obtain an oil
  6. stirringStirred 4 hours
  7. stirringstirred 10 minutes
  8. extractionthen extracted the aqueous 3× with methylene chloride
  9. customdried

Sources & evidence

ORD record
ord-66e98f318c424d1a82988f32c98ce735
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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