Sodium triacetoxyborohydride → HCID 90460303, compound

HRID 1053645Notes

Reaction equation

HRID 1053645 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[N:13]=[C:12]3C=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:28][N:29]([CH2:37][CH2:38][NH:39][CH3:40])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33].[BH-](OC(C)=O)(OC(C)=O)O[C:43](C)=O.[Na+]>ClCCCl>[CH3:28][N:29]([CH2:37][CH2:38][N:39]([CH3:43])[CH2:40][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][C:7]3[CH:26]=[CH:27][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH:10]=2)[N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[N:13]=1)[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 90461069HCID 90461069, compound

Product 1

HCID 90460303HCID 90460303, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (R/S) 5-(4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde (300 mg, 0.82 mmol, 1.00 equiv) and tert-butyl N-methyl-N-[2-(methylamino)ethyl]carbamate (170 mg, 0.90 mmol, 1.11 equiv) in 1,2-dichloroethane (40 mL) was added NaBH(OAc)3 (520 mg). The reaction was stirred at room temperature overnight and then quenched with 50 mL of water. The resulting mixture was extracted with 3×200 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-10% of ethyl acetate in petroleum ether to give 420 mg (95%) of (R/S) tert-butyl methyl(2-(methyl((5-(4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)methyl)amino)ethyl)carbamate as a colorless oil. 1H-NMR (400 MHz, CDCl3): δ 8.18 (m, 2H), 7.71-7.55 (m, 2H), 7.20-7.09 (m, 1H), 7.05-6.93 (m, 2H), 5.70-5.68 (m, 1H), 4.11-4.09 (m, 1H), 4.06-3.91 (m, 1H), 3.79-3.73 (m, 1H), 3.50-3.33 (m, 1H), 2.79 (s, 3H), 2.57-2.52 (m, 2H), 2.49-2.17 (m, 2H), 2.17-2.05 (m, 1H), 1.80-1.68 (m, 4H), 1.42 (s, 9H) ppm.

Workup

  1. customquenched with 50 mL of water
  2. extractionThe resulting mixture was extracted with 3×200 mL of ethyl acetate
  3. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified on a silica gel column
  6. washeluted with 0-10% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-654381289cac41b1a6d8ff827c6440a8
Source dataset
uspto-grants-2016_07
Patent number
US09394258B2

Reaction notes

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