Lithium borohydride → (R)-1-Hydroxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)propan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 2099794Notes

Reaction equation

HRID 2099794 reaction equation
[O:1]=[C:2]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C@H:21]([CH2:26][C:27]3[CH:35]=[C:34]([CH3:36])[C:33]4[C:29](=[CH:30][N:31]([CH2:37][O:38][CH3:39])[N:32]=4)[CH:28]=3)[C:22](OC)=[O:23])=[O:19])[CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[BH4-].[Li+]>O1CCCC1>[O:1]=[C:2]1[C:11]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C@H:21]([CH2:26][C:27]3[CH:35]=[C:34]([CH3:36])[C:33]4[C:29](=[CH:30][N:31]([CH2:37][O:38][CH3:39])[N:32]=4)[CH:28]=3)[CH2:22][OH:23])=[O:19])[CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57794695(R)-1-Methoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Product 1

HCID 57794702(R)-1-Hydroxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)propan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(R)-1-Methoxy-3-(2-(methoxymethyl)-7-methyl-2H-indazol-5-yl)-1-oxopropan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (0.70 g, 1.32 mmol) was dissolved in tetrahydrofuran (10 mL) and cooled to 0° C. To this solution was added lithium borohydride (0.12 g, 4.0 equiv). After 30 min, the ice bath was removed and the mixture stirred at room temperature for 3 h. The reaction mixture was diluted with ethyl acetate and carefully quenched with 10% citric acid. The organic layer was separated and washed with water (2×), brine (2×), dried over sodium sulfate, and concentrated to afford 0.68 g (99%) which was used without purification. Mass spec.: 505.3 (MH)+.

Workup

  1. customthe ice bath was removed
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. customcarefully quenched with 10% citric acid
  4. customThe organic layer was separated
  5. washwashed with water (2×), brine (2×)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto afford 0.68 g (99%) which
  9. customwas used without purification

Sources & evidence

ORD record
ord-1223238c132345f5bc50650c8ba5f23a
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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