Potassium sodium tartarate → HCID 86591135, compound

HRID 852848Notes

Reaction equation

HRID 852848 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:39])[NH:13][CH:14]([C:33](=[O:38])N(OC)C)[CH2:15][CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:17]1C)([CH3:10])([CH3:9])[CH3:8].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[C:7]([O:11][C:12](=[O:39])[NH:13][CH:14]([CH:33]=[O:38])[CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:17]=1)([CH3:8])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 86591136HCID 86591136, compound

Product 1

HCID 86591135HCID 86591135, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of LiAlH4 (143 mg, 3.76 mmol) in THF (5 mL) was added over 10 min to a solution of [2-(1-benzyl-2-methyl-2,3-dihydro-1H-indol-3-yl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (2 g, 4.32 mmol) in THF (35 mL) at −20° C. The reduction was complete in 15 min (silica gel, 50% EtOAc/petroleum ether, Rf 0.76). Saturated sodium potassium tartrate (10 mL) was added, and the solvent removed. Water was added and the residue extracted with Et2O. The Et2O was washed with brine, dried and filtered. Removal of the solvent gave the title compound (1.204 g, 93%). 1H NMR (CDCl3) δ 13C NMR (CDCl3) δ 200.3, 155.5, 137.3, 136.6, 128.7, 128.1, 127.6, 127.0, 126.7, 122.1, 119.5, 119.0, 109.8, 109.1, 79.9, 60.2, 49.9, 28.3, 25.2,

Workup

  1. customthe solvent removed
  2. additionWater was added
  3. extractionthe residue extracted with Et2O
  4. washThe Et2O was washed with brine
  5. customdried
  6. filtrationfiltered
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-57de9b3c3ae444bb87fff4194c1ae9a2
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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