Hydroxide → (+/-)-(3aR,6aS)-5-methyl-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole

HRID 473800Notes

Reaction equation

HRID 473800 reaction equation
[CH2:1]=[C:2]1[CH2:16][C@@H:5]2[CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8][C@@H:4]2[CH2:3]1.C(O)(C(F)(F)F)=O.[OH-]>CO>[CH3:1][C:2]1[CH2:3][C@H:4]2[CH2:8][NH:7][CH2:6][C@H:5]2[CH:16]=1

Participants

5

Procedure

(3aR,6aS)-tert-Butyl 5-methylenehexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (Tetrahedron 1993, 49(23), 5047-54) (114 mg, 0.51 mmol) was taken into a minimum of neat TFA and the solution was allowed to stand for 30 minutes at room temperature. The mixture was then concentrated and the residue taken into methanol and concentrated again then dried. The residue thus obtained was taken into methanol (5 mL) and basified using Bio-Rad AG-1X hydroxide form resin. The mixture was then filtered and concentrated and dried to give impure (±)-(3aR,6aS)-5-methyl-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole (93 mg) as an amorphous residue that was used without further purification.

Workup

  1. concentrationThe mixture was then concentrated
  2. concentrationconcentrated again
  3. customthen dried
  4. customThe residue thus obtained
  5. filtrationThe mixture was then filtered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-ea18ba9871dd4107b24c7c5aad76ffe4
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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