Dichloromethane → HCID 86640053, compound

HRID 2427261Notes

Reaction equation

HRID 2427261 reaction equation
ClCCl.[C:4]([O:8][C:9](=[O:25])[NH:10][C@H:11]1[CH2:24][C:14]2[NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]#N)=[CH:20][C:21]=3[C:13]=2[CH2:12]1)([CH3:7])([CH3:6])[CH3:5].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=[O:37].[Na+].[Na+]>C(OCC)(=O)C>[C:4]([O:8][C:9](=[O:25])[NH:10][C@H:11]1[CH2:24][C:14]2[NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH:22]=[O:37])=[CH:20][C:21]=3[C:13]=2[CH2:12]1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 21225700DiisobutylaluminumhydrideHCID 67253784HCID 67253784, compound

Product 1

HCID 86640053HCID 86640053, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine dichloromethane (15 ml) and (R)-[7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-carbamic acid tert-butyl ester (2 g, 6.73 mmol) and stir for 10 min under nitrogen at room temperature. Add diisobutylaluminum hydride (1 M solution in methylene chloride, 14.1 ml; 14.1 mmol) dropwise over 15 min. Add ethyl acetate (30 mL) to the reaction mixture and stir at room temperature for 1 h. Add a 20% aqueous solution of sodium tartrate (30 mL) and stir for 1 h at room temperature. Separate the organic layer and extract the aqueous layer with ethyl acetate (2×15 mL). Combine and dry (Na2SO4) organic layers, filter and concentrate to give 2.2 g [(R)-7-formyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-carbamic acid tert-butyl ester. Purify by chromatography on silica gel using methylene chloride/acetone (95/5) to give 1.3 g (64%). MS (m/z): 301 (M+1).

Workup

  1. customSeparate the organic layer
  2. extractionextract the aqueous layer with ethyl acetate (2×15 mL)
  3. dry with materialCombine and dry (Na2SO4) organic layers
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-89711845d3ae465bbcf1c7eecb28179e
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

Loading…