Lithium borohydride → HCID 67303821, compound

HRID 2061602Notes

Reaction equation

HRID 2061602 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:17]3[CH2:18][CH:19]4[N:24]([S:25]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)(=[O:27])=[O:26])[CH:23]([C:16]=3[CH:15]=[N:14]2)[CH2:22][CH:21]([C:35](OCC)=[O:36])[CH2:20]4)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([N:50]2[CH:54]=[C:53]3[CH:55]4[N:61]([S:62]([C:65]5[CH:70]=[CH:69][C:68]([Cl:71])=[CH:67][CH:66]=5)(=[O:64])=[O:63])[CH:59]([CH2:60][C:52]3=[N:51]2)[CH2:58][CH:57]([C:72](OCC)=[O:73])[CH2:56]4)(=[O:49])=[O:48])=[CH:43][CH:42]=1>C1COCC1.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([N:13]2[C:17]3[CH2:18][CH:19]4[N:24]([S:25]([C:28]5[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=5)(=[O:27])=[O:26])[CH:23]([C:16]=3[CH:15]=[N:14]2)[CH2:22][CH:21]([CH2:35][OH:36])[CH2:20]4)(=[O:12])=[O:11])=[CH:8][CH:9]=1.[Cl:40][C:41]1[CH:42]=[CH:43][C:44]([S:47]([N:50]2[CH:54]=[C:53]3[CH:55]4[N:61]([S:62]([C:65]5[CH:66]=[CH:67][C:68]([Cl:71])=[CH:69][CH:70]=5)(=[O:64])=[O:63])[CH:59]([CH2:60][C:52]3=[N:51]2)[CH2:58][CH:57]([CH2:72][OH:73])[CH2:56]4)(=[O:49])=[O:48])=[CH:45][CH:46]=1

Participants

7

Reactant 3

HCID 4148881Lithium borohydrideHCID 67302979HCID 67302979, compoundHCID 67308838HCID 67308838, compound

Product 2

HCID 67303821HCID 67303821, compoundHCID 68528112HCID 68528112, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium borohydride (10 mg, 0.516 mmol) was added to a solution of ethyl 1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carboxylate and ethyl 2,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazole-6-carboxylate (57) (0.151 mg, 0.258 mmol) in THF (1 mL) and the resulting solution was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc and washed with water. The organic phase was dried (Na2SO4), filtered and concentrated to give {1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazol-6-yl}methanol and {2,10-Bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazol-6-yl}methanol (58). MS (ESI) 542.0 (M+H).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dd9b940a47194e46a14ae227af0b0301
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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