Borane;tetrahydrofuran → HCID 66704472, compound

HRID 424566Notes

Reaction equation

HRID 424566 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][S:18][C:17]2[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:16]1=2)=O)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].B.O1CCCC1>O1CCCC1.C(OCC)(=O)C>[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][N:15]1[CH2:20][CH2:19][S:18][C:17]2[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:16]1=2)[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8]

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 66704710HCID 66704710, compound

Product 1

HCID 66704472HCID 66704472, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl 2-hydroxyethyl(2-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate (620 mg, 1.560 mmol) in tetrahydrofuran (5 mL) was added borane-tetrahydrofuran complex (1 M in tetrahydrofuran; 4.68 mL, 4.68 mmol), dropwise to avoid excessive bubbling. The mixture was then stirred at room temperature for 2 hours. The mixture was then quenched via the slow, dropwise addition of MeOH. The quenched reaction was then diluted with ethyl acetate and washed with saturated sodium carbonate (3×). The organic phase was dried, filtered, and concentrated giving a red oil (595 mg, 99%). 1H NMR (DMSO-d6) δ 7.59-7.44 (m, 1H), 7.38-7.32 (m, 1H), 7.22-7.13 (m, 1H), 4.74 (t, J=5.1 Hz, 1H), 3.69-3.62 (m, 2H), 3.61-3.39 (m, 6H), 3.29-3.17 (m, 2H), 3.15-3.04 (m, 2H), 1.31, 1.24 (2s, 9H); ESI-MS (m/z, %): 406 (M+Na, 55), 328 (40), 284 (100).

Workup

  1. customThe mixture was then quenched via the slow,
  2. additiondropwise addition of MeOH
  3. customThe quenched reaction
  4. washwashed with saturated sodium carbonate (3×)
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9f763c9f8ea84ecbad888485e0e08527
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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