Diisopropylethylamine → HCID 58598874, compound

HRID 1020321Notes

Reaction equation

HRID 1020321 reaction equation
C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[C:30](=[CH2:38])[CH:31]3[CH2:37][NH:36][CH2:35][CH:32]3[C:33]=2[CH:34]=1>C(Cl)Cl>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[CH:30]([CH3:38])[CH:31]3[CH2:37][NH:36][CH2:35][CH:32]3[C:33]=2[CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 67202659HCID 67202659, compound

Product 1

HCID 58598874HCID 58598874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl dicarbonate (0.43 g, 2.00 mmol) and DIEA (1.0 mL, 6.0 mmol) were added to a solution of 5-chloro-8-methylene-1,2,3,3a,8,8a-hexahydro-2-aza-cyclopenta[a]indene (2.0 mmol) in CH2Cl2 (10 mL) at 0° C. The reaction mixture was stirred for 2 hours at from 0° C. to room temperature, then quenched with aqueous HCl (10 mL, 0.1 M). The organic extracts were washed with brine, dried over MgSO4, and concentrated to afford the subtitle compound in quantitative yield. MS calculated for C17H20ClNO2+H: 306, observed: 306.

Workup

  1. customquenched with aqueous HCl (10 mL, 0.1 M)
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-48e22519e2814cefb98cbad628a0c288
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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