1,2-Diaminocyclohexane, trans- → HCID 59991040, compound

HRID 2421047Notes

Reaction equation

HRID 2421047 reaction equation
[CH2:1]1[CH2:6][C@@H:5]([NH2:7])[C@H:4]([NH2:8])[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O=[C:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:7][C@@H:5]1[CH2:6][CH2:1][CH2:2][CH2:3][C@H:4]1[NH:8][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59991040HCID 59991040, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (1R,2R)-cyclohexane diamine (20 g, 175 mmol) and sodium triacetoxyborohydride (25 g, 120 mmol) in dichloromethane (550 mL) was added with a solution of tert-butyl 4-oxopiperidine-1-carboxylate (18.4 g, 92 mmol) in dichloromethane (800 mL) dropwise over a period of 45 minutes and stirred at room temperature overnight. An aqueous solution of sodium bicarbonate (5%, 200 mL) was added to the reaction mixture, layers were separated, and the aqueous layer was extracted with dichloromethane (2×150 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the crude product which was purified by dry column vacuum chromatography to give the title compound as a pale yellow oil (18.0 g, 66%). 1H NMR (300 MHz, METHANOL-D4): δ ppm 3.99 (td, J=13.3, 3.3 Hz, 2H), 2.95-2.70 (m, 3H), 2.40-2.15 (m, 2H), 2.05 (m, 1H), 1.95-1.85 (m, 2H), 1.85-1.65 (m, 3H), 1.44 (s, 9H), 1.95-1.35 (m, 6H)

Workup

  1. customwere separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×150 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product which
  7. customwas purified
  8. customby dry column vacuum chromatography

Sources & evidence

ORD record
ord-1fa3c761937847b197c4c9bbbbc211bf
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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