Ethanol → HCID 59384346, compound

HRID 2357079Notes

Reaction equation

HRID 2357079 reaction equation
C(OC([NH:8][C:9]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:28]([C:41]([F:44])([F:43])[F:42])[CH:27]=2)=[CH:22][N:21]=1)(C(OCC)=O)[C:10](OCC)=[O:11])=O)(C)(C)C.[Li+].[BH4-].C(O)C>C1COCC1>[NH2:8][CH:9]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:28]([C:41]([F:44])([F:42])[F:43])[CH:27]=2)=[CH:22][N:21]=1)[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 4148881Lithium borohydrideHCID 59384371HCID 59384371, compound

Product 1

HCID 59384346HCID 59384346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl 2-(tert-butoxycarbonylamino)-2-(5-(4-(octyloxy)-3-(trifluoromethyl)-phenyl)-pyridin-2-yl)malonate 5a (110 mg, 0.176 mmol, 1.0 equiv) in THF (2.0 mL) was added LiBH4 (57 mg, 2.64 mmol, 15.0 equiv) at 0° C., followed by addition of ethanol (0.8 mL) carefully. The resultant was warmed up to room temperature for 10 minutes. LC-MS indicated the completion of the reaction. The reaction was terminated by addition of water. Extraction with ethyl acetate and the organic layer was washed with brine and dried over sodium sulfate and condensed. The residue (crude reduction product with significant decarboxylation) was treated with 2M HCl in THF to afford the title compound after preparative HPLC purification. MS (ESI, M+H+)=411.1; 1H NMR (400 MHz, DMSO-d6) δ 8.95 (d, 1H, J=2.4 Hz), 8.39 (s, 3H), 8.22 (dd, 1H, J=8.4 Hz, J=2.4 Hz), 8.01 (dd, 1H, J=8.4 Hz, J=2.0 Hz), 7.93 (d, 1H, J=2.0 Hz), 7.60 (d, 1H, J=8.4 Hz), 7.39 (d, 1H, J=9.2 Hz), 5.48 (br, 1H), 4.48 (br, 1H), 4.17 (t, 2H, J=6.0 Hz), 3.86-3.72 (m, 2H), 1.75 (m, 2H), 1.44 (m, 2H), 1.29 (m, 8H), 0.86 (t, 3H, J=6.8 Hz).

Workup

  1. customthe completion of the reaction
  2. customThe reaction was terminated by addition of water
  3. extractionExtraction with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate and condensed
  6. additionThe residue (crude reduction product with significant decarboxylation) was treated with 2M HCl in THF

Sources & evidence

ORD record
ord-6e622f65065d4445a4cdb2be63165fe8
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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