Triethylamine → HCID 178450647, compound

HRID 1717692Notes

Reaction equation

HRID 1717692 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[O:35](C(OC(C)(C)C)=O)[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:39]([O:38][C:36]([N:11]([C@H:8]1[CH2:9][CH2:10][C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)[CH:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=[O:35])([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178450643HCID 178450643, compound

Product 1

HCID 178450647HCID 178450647, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of butyl 1-[(trans-4-tert-butylcyclohexyl)amino]indane-5-carboxylate (1.0 g, 2.8 mmol) in CH2Cl2 (50 mL) was added Et3N (2.0 mL, 14.3 mmol), BOC2O (3.1 mL, 13.5 mmol) and catalytic amount of DMAP. After stirring at room temperature for 18 h, the reaction was quenched with saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer was extracted once with EtOAc (50 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. Chromatography (5% EtOAc in Hexane) gave butyl 1-[(tert-butoxycarbonyl)(trans-4-tert-butylcyclohexyl)amino]indane-5-carboxylate. HPLC/MS: m/z=416.3 (M−56+1), 438.3 (M−56+23), Rt=3.07 min. 1H NMR (CDCl3): δ 7.90 (1H, d, J=8.5 Hz), 7.89 (1H, s), 7.16 (1H, m), 4.75 (1H, br s), 4.35 (2H, t, J=6.5 Hz), 4.19 (1H, br s), 3.10-3.05 (1H, m), 2.97-2.87 (1H, m), 2.36 (2H, m), 1.91-1.77 (5H, m), 1.52 (2H, m), 1.07-1.00 (8H, m), 0.90 (9H, s), 0.89 (9H, s).

Workup

  1. customthe reaction was quenched with saturated aqueous NaHCO3 (50 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted once with EtOAc (50 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a039679286074c39bbb2c896e827959d
Source dataset
uspto-grants-2010_09
Patent number
US07803951B2

Reaction notes

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