2-Methylbenzaldehyde → HCID 86584839, compound

HRID 458320Notes

Reaction equation

HRID 458320 reaction equation
[CH:1]1[C:10]2C(=CC=[CH:8][CH:9]=2)C=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][C@H:17]([S:19]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:16][C@H:15]1[CH2:39][NH2:40])(=[O:13])=[O:12].[C:41]1([CH3:49])[C:42]([CH:47]=O)=[CH:43][CH:44]=[CH:45][CH:46]=1.Cl[Sn]Cl.[BH3-]C#N.[Na+]>CO>[CH3:47][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[CH2:49][NH:40][CH2:39][C@H:15]1[N:14]([S:11]([C:2]2[CH:3]=[CH:8][C:9]3[C:10](=[CH:10][CH:1]=[CH:2][CH:3]=3)[CH:1]=2)(=[O:13])=[O:12])[CH2:18][C@H:17]([SH:19])[CH2:16]1

Participants

6

Reactant 4

HCID 107222-MethylbenzaldehydeHCID 24479Stannous ChlorideHCID 5003444Sodium cyanoborohydrideHCID 23519861HCID 23519861, compound

Product 1

HCID 86584839HCID 86584839, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

250 mg (0.56 mmol) (2S,4R)-C-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-yl]-methylamine and 58 μl (0.5 mmol) o-tolualdehyde in 1 ml MeOH were treated with a solution of 57 mg (0.3 mmol, 0.6 eq) SnCl2 and 38 mg (0.6 mmol, 1.2 eq) NaBH3CN in 1 ml MeOH at room temperature and subsequent cleavage of the protecting group (Method 3) gave (3R,5S)-5-[(2-methyl-benzylamino)-methyl]-1-(naphthalene-2-sulfonyl)-pyrrolidine-3-thiol as white solid, mp 122° C., MS: 427 (MH+).

Sources & evidence

ORD record
ord-2101decb5e954e53847402c4ec9dd3e4
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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