Sodium triacetoxyborohydride → HCID 69482688, compound

HRID 2364439Notes

Reaction equation

HRID 2364439 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:4][CH:5]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:7]=1.[CH3:21][N:22]([CH2:33][CH:34]=O)[C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(Cl)Cl>[F:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][C:6]2[CH:7]=[C:2]([NH:1][CH2:34][CH2:33][N:22]([CH3:21])[C:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:32])[C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:4][CH:5]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydride2×HCID 12010768Benzyl N-methyl-N-(2-oxoethyl)carbamateHCID 42637772Ethyl 3-amino-5-(4-fluorobenzyl)picolinate

Product 1

HCID 69482688HCID 69482688, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate (1.78 g, 6.5 mmol) and phenylmethyl methyl(2-oxoethyl)carbamate (2.58 g, 12.4 mmol) under nitrogen in glacial acetic acid (300 mL) was treated with sodium triacetoxyborohydride (2.56 g, 12.1 mmol) at ambient temperature overnight. Concentrated the reaction in vacuo then redissolved in glacial acetic acid (100 mL) and treated with another 1 g of sodium triacetoxyborohydride at ambient temperature for 2 h. The reaction was evaporated in vacuo and the residue was chromatographed on silica gel eluting with 98:2-95:5 CH2Cl2:EtOAc to provide a clear viscous oil. The oil was dissolved in CH2Cl2, washed with saturated K2CO3, water, and brine, dried over Na2SO4, filtered and evaporated in vacuo to afford the product as a yellow viscuos oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.27 (t, J=7.09 Hz, 3 H), 2.87 (d, J=5.90 Hz, 3 H), 3.34-3.51 (m, 4 H), 3.89 (d, J=20.22 Hz, 2 H), 4.24 (q, J=7.16 Hz, 2 H), 5.02 (d, J=23.16 Hz, 2 H), 7.09 (t, J=8.84 Hz, 2 H), 7.18-7.39 (m, 7 H), 7.66 (d, J=16.00 Hz, 1 H), 7.77 (s, 1 H); ES+ MS: 466 (M+H+).

Workup

  1. concentrationConcentrated
  2. customthe reaction in vacuo
  3. customThe reaction was evaporated in vacuo
  4. customthe residue was chromatographed on silica gel eluting with 98:2-95:5 CH2Cl2
  5. customEtOAc to provide a clear viscous oil
  6. washwashed with saturated K2CO3, water, and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-71b65f2b47ff426b8bee04b8fa0b2f99
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…