Sodium borohydride → HCID 178521617, compound

HRID 2076379Notes

Reaction equation

HRID 2076379 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:4](=[O:21])[C@@H:5]2[CH2:20][C@@:8]3([CH2:19][C:18]4[C:14]5[N:15]=[N:16][NH:17][C:13]=5[CH:12]=[CH:11][C:10]=4[C:9]=13)[CH2:7][CH2:6]2.[BH4-].[Na+]>C(O)C>[F:22][C:2]([F:1])([F:23])[C:3]1[C@H:4]([OH:21])[C@H:5]2[CH2:20][C@:8]3([CH2:19][C:18]4[C:14]5[N:15]=[N:16][NH:17][C:13]=5[CH:12]=[CH:11][C:10]=4[C:9]=13)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178516316HCID 178516316, compound

Product 1

HCID 178521617HCID 178521617, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (8S,10aR)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanocyclohepta[1,2]indeno[4,5-d][1,2,3]triazol-7(8H)-one (6.0 mg, 0.019 mmol) in ethanol (0.5 mL) was cooled to 0° C. and solid sodium borohydride (2.8 mg, 0.075 mmol) was added. After 1 hour, the reaction was quenched by addition of water and was directly loaded onto a reverse phase HPLC column eluting with MeCN/water (10:90 to 90:10). The fraction containing the desired product was concentrated under vacuum and then partitioned between ethyl acetate and pH 7 phosphate buffer. The organic phase was washed with brine and dried over MgSO4. The solution was filtered and evaporated under vacuum and the residue was lyophilized from benzene to give (7R,8R,10aS)-6-(trifluoromethyl)-3,7,8,9,10,11-hexahydro-8,10a-methanocyclohepta[1,2]indeno[4,5-d][1,2,3]triazol-7-ol as a white solid.

Workup

  1. customthe reaction was quenched by addition of water
  2. washeluting with MeCN/water (10:90 to 90:10)
  3. additionThe fraction containing the desired product
  4. concentrationwas concentrated under vacuum
  5. custompartitioned between ethyl acetate and pH 7 phosphate buffer
  6. washThe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationThe solution was filtered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-1e1ff52b32c848c79ae8174fd4bbddbf
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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