Tetrahydrofuran → HCID 68182913, compound

HRID 2274984Notes

Reaction equation

HRID 2274984 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:11](=[O:18])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.O=[CH:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C1COCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:12]3([CH2:13][CH2:14][N:15]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:16][CH2:17]3)[C:11](=[O:18])[NH:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 69488998HCID 69488998, compound

Product 1

HCID 68182913HCID 68182913, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing 0.25 g (1.0 mmol) of (S)-4-(4-fluorophenyl)-2,8-diazaspiro[4.5]decan-1-one, 0.2 g (1.41 mmol) of tert-butyl 2-oxoethylcarbamate, 2 mL of THF, 1 mL of DCM, and 1 g (2.5 mmol) of MP-sodium triacetoxyborohydride resin was rotated overnight. The reaction mixture was filtered and the solvents were removed under reduced pressure. The residue was subjected to silica gel chromatography to give 131 mg (33%) of (S)-tert-butyl 2-(4-(4-fluorophenyl)-1-oxo-2,8-diazaspiro[4.5]decan-8-yl)ethylcarbamate as a colorless oil: 1HNMR (400 MHz, CD3OD) δ ppm 7.35-7.32 (m, 2H), 7.12-7.07 (m, 2H), 3.68 (dd, 1H, J=10.4 and 7.6 Hz), 3.57 (dd, 1H, J=10.4 and 6.4 Hz), 3.32-3.28 (m, 3H), 3.11-3.08 (m, 2H), 2.87-2.84 (m, 3H), 2.02-1.80 (m, 4H), 1.41 (s, 9H), and 1.34-1.27 (m, 2H); LCMS m/z: 392.3 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-c9c2de5b101f46d6af1db69e703181b8
Source dataset
uspto-grants-2015_09
Patent number
US09127005B2

Reaction notes

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